There has been ongoing controversy over the way high-stakes standardized exams impact class inequality and race/ethnic diversity. However, relatively few studies have examined the potential consequences for gender inequality in access to selective institutions. There is a significant gender gap in students who retake the high-stakes entrance exam when they fail, especially when admissions opportunities are extremely limited. Drawing upon previous studies, I examine how the seemingly fair meritocratic selection in the transition from upper-secondary to higher education in Japan, where only one in five undergraduate students in the nation’s top university are women, contributes to the persistence of women’s “leaky pipeline” to selective colleges. The results from longitudinal surveys of high schoolers and their parents reveal that parents’ educational expectations and psychological traits relevant to competitive environments are not associated with the gender gap in exam-retaking. Instead, the positive association between aspirations to attend a selective college and exam-retaking is significantly reduced for women, suggesting that men and women with similar competitive academic aspirations are treated differently. These results provide important evidence to reduce gender inequality in science, politics, and the labor market.